US5741817A - Use of low molecular weight amino acids in ophthalmic compositions - Google Patents
Use of low molecular weight amino acids in ophthalmic compositions Download PDFInfo
- Publication number
- US5741817A US5741817A US08/575,740 US57574095A US5741817A US 5741817 A US5741817 A US 5741817A US 57574095 A US57574095 A US 57574095A US 5741817 A US5741817 A US 5741817A
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- United States
- Prior art keywords
- molecular weight
- composition
- low molecular
- compositions
- glycine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
- A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
- A61L12/14—Organic compounds not covered by groups A61L12/10 or A61L12/12
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
Definitions
- the present invention relates to the field of ophthalmology. More specifically, the invention relates to the use of glycine and other low molecular weight amino acids in products for treating contact lenses, as well as other ophthalmic products.
- the amino acids described herein may serve several useful purposes in such compositions, but have been found to be particularly useful in enhancing the activity of antimicrobial preservatives.
- Ethylenediaminetetraacetic acid and the monosodium, disodium and trisodium salts thereof have been widely used for many years in ophthalmic products, particularly products for treating contact lenses. It has been utilized in such products for various purposes, but particularly for its supplemental antimicrobial activity and as a chelating agent.
- EDTA Ethylenediaminetetraacetic acid and the monosodium, disodium and trisodium salts thereof
- compositions for treating contact lenses such as chlorine, iodine and other oxidizing agents.
- the present invention is based on a new use of glycine and other low molecular weight amino acids.
- the present inventors have found that such amino acids enhance the activity of antimicrobial preservatives, and are also useful as chelating agents.
- the low molecular weight amino acids can also serve as buffers and tonicity agents. Based on these properties, glycine and the other amino acids described herein can be utilized in various types of ophthalmic compositions, particularly compositions for treating contact lenses, such as disinfectants, cleaners, comfort drops and rewetting drops, instead of EDTA.
- the low molecular weight amino acids are particularly useful in preserved saline solutions which are utilized for rinsing and storing contact lenses.
- the low molecular weight amino acids which may be utilized in the present invention have a molecular weight in the range of from about 75 to about 250.
- the following compounds are representative of the low molecular weight amino acids which may be utilized in the present invention:
- Amino acids which include alpha (a) carboxylic acid groups are preferred.
- the amount of amino acid utilized will depend on the molecular weight of the amino acid(s) selected. In general, one or more of the above-described amino acids will be utilized in a concentration of from about 0.01 to about 7.5 percent by weight/volume (“w/v%").
- the preferred amino acid for use in the present invention is glycine.
- Glycine is a relatively simple, low molecular weight amino acid. It is also known as "aminoacetic acid".
- the amount of glycine utilized in the compositions of the present invention will vary depending on the type of composition in which it is contained, and the function of glycine in the composition. In general, compositions which contain glycine for purposes of enhancing the antimicrobial activity of the compositions will contain glycine in an amount of from about 0.01 to about 2.5 w/v%., preferably from about 0.1 to about 1.0 w/v%. Similar amounts of glycine will be utilized to perform the other functions mentioned above.
- low molecular weight amino acids may be combined with various ingredients conventionally utilized in ophthalmic products, particularly products for treating contact lenses. More specifically, these compounds may be utilized to enhance the antimicrobial activity of an ophthalmic composition, so as to preserve the composition against microbial contamination. Additionally, such compounds contribute to the tonicity, chelating and buffering properties of the composition.
- the low molecular weight amino acids described herein may be included in various types of ophthalmic compositions to enhance antimicrobial activity, or for the other purposes mentioned above.
- the types of compositions include: ophthalmic pharmaceutical compositions, such as topical compositions used in the treatment of glaucoma, infections, allergies or inflammation; compositions for treating contact lenses, such as cleaning products and products for enhancing the ocular comfort of patients wearing contact lenses; and various other types of compositions, such as ocular lubricating products, artificial tears, astringents, and so on.
- the compositions may be aqueous or nonaqueous, but will generally be aqueous.
- compositions of the present invention may contain one or more antimicrobial agents to preserve the compositions from microbial contamination.
- the compositions may contain the antimicrobial agent known as POLYQUAD®; the use of this agent as a preservative in ophthalmic compositions is described in U.S. Pat. No. 4,525,346 (Stark). The entire contents of the Stark 346 patent are hereby incorporated in the present specification by reference.
- Additional examples of antimicrobial agents include chlorhexidine, alexidine, hexetidine, polyhexamethylene biquanide, benzalkonium chloride, benzododecinum bromide, and other antimicrobial agents utilized as antimicrobial perservatives in ophthalmic compositions.
- the inclusion of one or more of the above-described low molecular weight amino acids in ophthalmic compositions containing such antimicrobial preservatives enhances the overall antimicrobial activity of the compositions.
- compositions may also contain a wide variety of other ingredients, such as tonicity agents (e.g., sodium chloride or mannitol), surfactants (e.g., alkyl ethoxylates and polyoxyethylene/polyoxypropylene copolymers), viscosity adjusting agents (e.g., hydroxypropyl methyl cellulose and other cellulose derivatives) and buffering agents (e.g., borates, citrates, phosphates and carbonates).
- tonicity agents e.g., sodium chloride or mannitol
- surfactants e.g., alkyl ethoxylates and polyoxyethylene/polyoxypropylene copolymers
- viscosity adjusting agents e.g., hydroxypropyl methyl cellulose and other cellulose derivatives
- buffering agents e.g., borates, citrates, phosphates and carbonates.
- borate/mannitol buffering system is preferred. The use
- compositions of the present invention preferably do not contain EDTA.
- compositions will be formulated so as to be compatible with the eye and/or contact lenses to be treated with the compositions.
- the ophthalmic compositions intended for direct application to the eye will be formulated so as to have a pH and tonicity which are compatible with the eye. This will normally require a buffer to maintain the pH of the composition at or near physiologic pH (i.e., 7.4) and may require a tonicity agent to bring the osmolality of the composition to a level at or near 280-320 milliosmoles per kilogram (“mOsm/kg").
- the formulation of compositions for disinfecting and/or cleaning contact lenses will involve similar considerations, as well as considerations relating to the physical effect of the compositions on contact lens materials and the potential for binding or absorption of the components of the composition by the lens.
- composition represents an example of a saline solution which does not contain any conventional antimicrobial preservatives.
- This composition may be prepared by sequentially adding the ingredients to a portion of the distilled water and stirring the solution until each of the ingredients has dissolved. When all of the ingredients have been dissolved, the solution is brought to final volume by the addition of the remainder of the water, and the pH is adjusted, if necessary.
- the solution has an osmolality of 295 mOsm/kg. It has been tested and found to meet the United States Pharmacopeia (“USP") and United States Food and Drug Administration (“FDA”) requirements for preservative effectiveness; those requirements are referred to below by means of the term "PET", which is an abbreviation for "preservative effectiveness test”.
- USP United States Pharmacopeia
- FDA United States Food and Drug Administration
- PET is an abbreviation for "preservative effectiveness test”.
- the above-described composition is referred to below as "Formulation A”.
- the antimicrobial efficacy of Formulation A was evaluated. More specifically, the antimicrobial activity this saline solution was evaluated by inoculating 20 milliliters ("ml") of the solution with 0.1 ml of a microbial suspension. The final concentration was approximately 106 colony forming units per ml. At each time pull, the number of survivors was determined by taking a 1 ml aliquot of the test sample, serially diluting in 9 ml of saline at selected time intervals and preparing pour plates of SCDA. The bacteria and yeast plates were incubated at 30° C. to 35° C. for two to three days. The mold plates were incubated at 20° to 25° C. for five days. The results are presented in Table 1 below.
- Formulation B represents an example of a saline solution containing a relatively high concentration of glycine in a borate buffer.
- This solution was prepared by means of a procedure similar to the procedure described in Example 1 above.
- the pH of the solution was 7.6 and the osmolality was 295 mOsm/kg.
- the antimicrobial activity of Formulation B was evaluated against a gram negative and a gram positive bacteria by means of the procedures described in Example 2.
- the solution showed a 2.2 log reduction against S. aureus and a 3.8 log reduction against P. aeruginosa at 7 days.
- compositions were tested to determine if EDTA could simply be eliminated from saline solutions; the compositions were prepared by means of procedures similar to the procedure described in Example 1 above:
- Formulation C has a pH of 7.7 and osmolality of 299 mOsm/kg
- Formulation D has a pH of 7.7 and osmolality of 294 mOsm/kg
- Formulation E has a pH of 7.3 and osmolality of 305 mOsm/kg.
- composition represents an example of the preserved saline solutions of the present invention, wherein a low molecular weight amino acid is utilized to augment the activity of a conventional antimicrobial preservative.
- This composition may be prepared by sequentially adding the listed ingredients to 90 ml of purified water and stirring until each ingredient has dissolved. The pH is adjusted to 7.4 and the volume is adjusted to 100 ml.
- the low molecular weight amino i.e., glycine
- the above composition is an example of a composition for lubricating contact lenses or increasing the comfort of contact lenses when worn by patients.
- the composition is prepared in two parts and then recombined.
- polyvinyl alcohol and hydroxyethyl cellulose are dispersed in 40 ml of purified water at a temperature of 50°-70° C., and then allowed to hydrate and cool to room temperature.
- the solution is then Polish filtered using a 5-20 micrometer ("pm") membrane filter and autoclaved.
- the remaining ingredients are dissolved in 50 ml of purified water. This solution is then sterile filtered using a 0.22 ⁇ m membrane filter into a sterile receiving container.
- the first part and the second part are then combined aseptically and the pH of the resulting solution is adjusted to 7.4.
- the volume of the solution is then brought to 100 ml with purified water.
- the solution has an osmolality of 230-260 mOsm/kg.
- a low molecular weight amino acid in this composition enhances the antimicrobial activity of the composition, and also eliminates the need for an additional tonicity agent, such as sodium chloride.
- the above composition is an example of a multi-purpose solution for cleaning, disinfecting and storing contact lenses.
- the composition was prepared by sequentially adding the ingredients to 90 ml of purified water and stirring until each ingredient was dissolved.
- the pH of the resulting solution was adjusted to 7.4, and the volume was adjusted to 100 ml with purified water.
- the low molecular weight amino acid performs the same function in this composition as in the other compositions described above.
Abstract
Description
______________________________________ L-Alanine β-Alanine α-Aminoadipic Acid α-Aminobutyric Acid γ-Aminobutyric Acid α-Aminoisobutyric Acid Arginine Asparagine Aspartic Acid Citrulline Creatine Glutamic Acid Glycine Histidine Cystine Leucine Lysine Norleucine Ornithine Phenylalanine Phophoserine Sarcosine Threonine Valine ______________________________________
______________________________________ Ingredient Concentration (w/v %) ______________________________________ Boric Acid 1.0 Mannitol 1.5 Glycine 0.75 Pationic 138C 0.01 KOH/HCl pH 7.4 Purified Water q.s. ______________________________________
TABLE 1 ______________________________________ Antimicrobial Activity of Formulation A Against PET Microorganisms Organism Time Log Reduction ______________________________________ A. niger 7 Days 2.5 14 Days 1.5 21 Days 1.5 28 Days 1.4 35 Days 1.6 C. albicans 7 days 3.7 14 Days 4.7 21 Days 3.2 28 Days 4.5 P. aeruginosa 7 Days 3.5 14 Days 5.2 21 Days 3.1 28 Days 3.8 E. coli 7 Days 3.5 14 Days 4.9 21 Days 3.3 28 Days 3.9 S. aureus 7 Days 5.0 14 Days 5.0 21 Days 4.9 28 Days 4.6 ______________________________________
______________________________________ Ingredient Concentration (w/v %) ______________________________________ Boric Acid 0.442 Sodium Borate 0.0875 Glycine 1.61 Pationic 138C 0.01 Purified Water q.s. ______________________________________
______________________________________ Concentration (w/v %) Ingredient Formulation C Formulation D Formulation E ______________________________________ Boric Acid 0.442 0.442 0.442 Sodium Borate 0.0875 0.0875 0.0874 Sodium Chloride 0.675 0.675 0.675 Pationic 138C -- 0.01 0.01 Disodium Edetate -- -- 0.1 Purified Water q.s q.s. q.s. ______________________________________
______________________________________ Antimicrobial Activity (i.e., Log Reduction at Day 7) Against PET Microorganisms Formulation C Formulation D Formulation E ______________________________________ A. niger 1.8 1.9 1.0 P. aeruginosa 0.0 0.4 4.1 S. aureus 1.6 4.1 5.0 ______________________________________
______________________________________ Ingredient Concentration (w/v %) ______________________________________ Boric acid 0.35 Sodium borate 0.11 Mannitol 1.5 Glycine 0.75 Polyquad 0.001 Purified water q.s. ______________________________________
______________________________________ Ingredient Concentration (w/v %) ______________________________________ Polyvinyl alcohol 0.75 Hydroxyethyl cellulose 0.28 Boric acid 0.35 Sodium borate 0.11 Mannitol 2.0 Glycine 0.5 Polyquad ™ 0.001 Purified water q.s. ______________________________________
______________________________________ Ingredient Concentration (w/v %) ______________________________________ Polaxamine 0.25 Boric acid 0.5 Mannitol 1.5 Sodium chloride 0.15 Glycine 0.25 Polyhexamethylene 0.0005 biquanide Purified water q.s. ______________________________________
Claims (7)
______________________________________ Ingredient Concentration (w/v %) ______________________________________ Boric Acid 1.0 Mannitol 1.5 Glycine 0.75 Pationic 138C 0.01 KOH/HCl pH 7.4 Purified Water q.s.. ______________________________________
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/575,740 US5741817A (en) | 1994-07-22 | 1995-12-18 | Use of low molecular weight amino acids in ophthalmic compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US27932494A | 1994-07-22 | 1994-07-22 | |
US08/575,740 US5741817A (en) | 1994-07-22 | 1995-12-18 | Use of low molecular weight amino acids in ophthalmic compositions |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US27932494A Continuation | 1994-07-22 | 1994-07-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
US5741817A true US5741817A (en) | 1998-04-21 |
Family
ID=23068484
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/575,740 Expired - Lifetime US5741817A (en) | 1994-07-22 | 1995-12-18 | Use of low molecular weight amino acids in ophthalmic compositions |
Country Status (3)
Country | Link |
---|---|
US (1) | US5741817A (en) |
AU (1) | AU3070395A (en) |
WO (1) | WO1996003158A1 (en) |
Cited By (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6146622A (en) * | 1998-10-27 | 2000-11-14 | Alcon Laboratories, Inc. | Use of certain anionic amino acid based surfactants to enhance antimicrobial effectiveness of topically administrable pharmaceutical compositions |
US6180093B1 (en) * | 1996-09-20 | 2001-01-30 | Bausch & Lomb Incorporated | Method and composition for rewetting contact lenses and relieving eye dryness |
US6211238B1 (en) | 1998-10-27 | 2001-04-03 | Alcon Laboratories, Inc. | Preservative system for topically administrable pharmaceutical compositions |
US6284749B1 (en) | 1998-10-27 | 2001-09-04 | Alcon Manufacturing, Ltd. | Preservative system for topically administrable pharmaceutical compositions containing a fatty acid/amino acid soap |
US6444710B1 (en) | 1998-10-27 | 2002-09-03 | Alcon Manufacturing, Ltd. | Use of certain fatty acid/amino acid soaps to enhance antimicrobial effectiveness of topically administrable pharmaceutical compositions |
US20030153622A1 (en) * | 2001-09-17 | 2003-08-14 | Menicon Co., Ltd. | Ophthalmic solution and contact lens solution |
US6617291B1 (en) | 2001-11-08 | 2003-09-09 | Francis X. Smith | Ophthalmic and contact lens solutions |
US6620797B2 (en) | 2000-12-21 | 2003-09-16 | Alcon, Inc. | Artificial tear composition containing a combination of three demulcents |
US6624203B1 (en) | 2001-11-08 | 2003-09-23 | Francis X. Smith | Nucleic acid bases used in ophthalmic solutions |
US20030190258A1 (en) * | 2000-11-04 | 2003-10-09 | Smith Francis X. | Ophthalmic and contact lens solutions using low molecular weight amines |
US20040241206A1 (en) * | 2001-12-21 | 2004-12-02 | Ketelson Howard Allen | Use of nanoparticles as carriers for biocides in ophthalmic compositions |
US20050002970A1 (en) * | 2001-12-21 | 2005-01-06 | Ketelson Howard Allen | Inorganic nanopartices to modify the viscosity and physical properties of ophthalmic and otic compositions |
US20050003014A1 (en) * | 2001-12-21 | 2005-01-06 | Ketelson Howard Allen | Use of synthetic inorganic nanoparticles as carriers for ophthalmic and otic drugs |
US20050042198A1 (en) * | 1999-11-04 | 2005-02-24 | Smith Francis X. | Ophthalmic and contact lens wetting solutions |
US20050124702A1 (en) * | 2003-12-09 | 2005-06-09 | Alcon, Inc. | Use of organic buffering agents to enhance the antimicrobial activity of pharmaceutical compositions |
US20050154065A1 (en) * | 2003-12-09 | 2005-07-14 | Alcon, Inc. | Use of bis-amines to enhance the antimicrobial activity of aqueous compositions |
US20060078626A1 (en) * | 2000-11-08 | 2006-04-13 | Bioconcept Laboratories | Opthalmic and contact lens solutions with a peroxide source and a cationic polymeric preservative |
US20060127496A1 (en) * | 2000-11-08 | 2006-06-15 | Bioconcept Laboratories | L-histidine in ophthalmic solutions |
US20060142169A1 (en) * | 2000-11-08 | 2006-06-29 | Bioconcept Laboratories | Ophthalmic and contact lens solutions containing simple saccharides as preservative enhancers |
US20060141059A1 (en) * | 2004-12-27 | 2006-06-29 | Alcon, Inc. | Self-preserved ophthalmic pharmaceutical compositions containing tobramycin |
US20060148665A1 (en) * | 2000-11-08 | 2006-07-06 | Bioconcept Laboratories | Ophthalmic and contact lens solutions containing forms of vitamin b |
WO2007048523A1 (en) * | 2005-10-26 | 2007-05-03 | Solartium Enterprises Limited | Ophthalmic pharmaceutical compositions based on amino acids and sodium hyaluronate |
US20070098813A1 (en) * | 2000-11-08 | 2007-05-03 | Fxs Ventures, Llc | Ophthalmic and contact lens solutions with a peroxide source and a preservative |
US20070098818A1 (en) * | 2000-11-08 | 2007-05-03 | Fxs Ventures, Llc | Ophthalmic and contact lens solutions containing simple saccharides as preservative enhancers |
US20070104744A1 (en) * | 2000-11-08 | 2007-05-10 | Fxs Ventures, Llc | Ophthalmic and contact lens solutions containing forms of vitamin b |
US20080075790A1 (en) * | 2006-09-21 | 2008-03-27 | Alcon Manufacturing, Ltd. | Self preserved aqueous pharmaceutical compositions |
US20080095754A1 (en) * | 2006-10-18 | 2008-04-24 | Burke Susan E | Ophthalmic compositions comprising diglycine |
US20080095863A1 (en) * | 2006-10-24 | 2008-04-24 | Alcon Manufacturing Ltd. | 2-pyrrolidone derivatives for preservation of ophthalmic, otic and nasal compositions |
US20080096966A1 (en) * | 2006-10-18 | 2008-04-24 | Burke Susan E | Ophthalmic compositions containing diglycine |
US20080093247A1 (en) * | 2006-10-24 | 2008-04-24 | Alcon Manufacturing Ltd. | Packaging materials for formulations containing 2-pyrrolidone derivatives |
US20080167246A1 (en) * | 2003-04-15 | 2008-07-10 | Bioconcept Laboratories | Ophthalmic and Contact Lens Solutions Containing Peptides as Preservative |
US20080261915A1 (en) * | 2005-10-26 | 2008-10-23 | Solartium Llc | Wound-Healing Pharmaceutical Compositions in the Form of a Sterile Powder Based on Amino Acids and Sodium Hyaluronate |
US20080287392A1 (en) * | 2005-10-26 | 2008-11-20 | Solartium Llc | Wound-Healing Pharmaceutical Compositions in the Form of a Cream Based on Amino Acids and Sodium Hyaluronate |
US20090074879A1 (en) * | 2005-08-11 | 2009-03-19 | Gianluca Braguti | Wound-Healing Composition |
US20090232763A1 (en) * | 2008-03-17 | 2009-09-17 | Kabra Bhagwati P | Aqueous pharmaceutical compositions containing borate-polyol complexes |
US20090234004A1 (en) * | 2008-03-17 | 2009-09-17 | Kabra Bhagwati P | Pharmaceutical compositions having desirable bioavailability |
US20090247469A1 (en) * | 2008-03-25 | 2009-10-01 | Burke Susan E | Ophthalmic compositions comprising a dipeptide |
US20100021561A1 (en) * | 2006-09-21 | 2010-01-28 | Chowhan Masood A | Self-preserved aqueous pharmaceutical compositions |
US20100021562A1 (en) * | 2006-09-28 | 2010-01-28 | Chowhan Masood A | Self preserved aqueous pharmaceutical compositions |
US20100324031A1 (en) * | 2009-06-19 | 2010-12-23 | Kabra Bhagwati P | Aqueous pharmaceutical compositions containing borate-polyol complexes |
WO2011053569A1 (en) * | 2009-10-26 | 2011-05-05 | Inotek Pharmaceuticals Corporation | Ophthalmic formulation and method of manufacture thereof |
US8324171B1 (en) | 2012-02-06 | 2012-12-04 | Bausch & Lomb Incorporated | Ophthalmic compositions containing diglycine |
US8664180B2 (en) | 2012-02-06 | 2014-03-04 | Bausch & Lomb Incorporated | Ophthalmic compositions containing diglycine |
US9308264B2 (en) | 2000-11-08 | 2016-04-12 | Fxs Ventures, Llc | Ophthalmic contact lens solutions containing forms of vitamin B |
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DK1190718T3 (en) * | 1996-12-13 | 2006-09-25 | Alcon Lab Inc | Ophthalmic compositions comprising amino alcohols |
KR100366676B1 (en) * | 1996-12-13 | 2003-01-14 | 알콘 래보레이토리스, 인코퍼레이티드 | Use of low molecular weight amino alcohols in ophthalmic compositions |
WO2006138709A2 (en) | 2005-06-17 | 2006-12-28 | Regenerx Biopharmaceuticals, Inc. | Lkktet and/or lkktnt peptide compositions and methods |
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- 1995-07-17 AU AU30703/95A patent/AU3070395A/en not_active Abandoned
- 1995-07-17 WO PCT/US1995/008937 patent/WO1996003158A1/en active Application Filing
- 1995-12-18 US US08/575,740 patent/US5741817A/en not_active Expired - Lifetime
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Cited By (87)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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WO1996003158A1 (en) | 1996-02-08 |
AU3070395A (en) | 1996-02-22 |
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